I wanted to comment on two of @charliecompany34 ‘s food recommendations:
Al’s Italian Beef – Yes! The original Al’s is actually on Taylor street in little Italy between the U of I Circle campus and the big cluster of hospitals on the near west side. I didn’t know they were in River North too, but the sandwiches are to die for, and try the handcut fries as well.
Garrett’s popcorn – another whole hearted yes. Expensive and unhealthy, but junkfood ambrosia. It’s intensely flavored, so you can get away with small bags, but you’ll probably wish you had gotten more once you taste it. Try both the cheese corn and the caramel corn. True believers get both mixed in one bag. There are Garrett’s scattered through downtown, there’s also one at Navy Pier and even one in the O’Hare airport.
If you don’t have access to “real” Gyros in your hometown, I would also be on the lookout for that. By real, I mean the kind where they carve the meat off a large roast on a vertical spit with flames on one side. Here in Eugene, gyros are prepackaged slices that get heated just before serving – not the same, so gyros is always on my want list when I go back to Chicago to see family.
The Chicago Cultural Center downtown is free and worth a look. http://www.chicagoculturalcenter.org/
They have the worlds largest Tiffany stained glass dome in the world, and rotating art exhibits. Also, music and theater performances also with free admission.
Navy Pier is another spot to consider checking out. The shopping is not that great, but it’s a fun place to hang out and enjoy the lakefront, there’s fireworks on the weekends, a ferris wheel, and if you want to splurge, you can rent bikes or segways or take a short cruise onto the lake.
And if you’re an architecture buff, try to get out to Oak Park, a near west suburb for a tour of the world’s largest collection of Frank Lloyd Wright structures.
http://www.oprf.com/flw/